The Gen Mess with Tess

No one really warns you how psychologically hard early career can be.You learn how to write a resume, interview, and get hired, but almost no one explains what it feels like once you’re inside the workplace. You're being evaluated constantly, questioning yourself, guessing the rules, and trying to build confidence without experience.In this episode of The Gen Mess with Tess, Tess Brigham explains why the beginning of your career can feel so mentally intense, and why that experience is often misunderstood. She breaks down the psychological weight of uncertainty, self-doubt, comparison, unclear expectations, and why many young professionals incorrectly assume they are the problem when they are often responding normally to a demanding environment.Tess also addresses something leaders need to hear clearly: being early career does not mean someone should tolerate unhealthy behavior, poor emotional regulation, or unclear leadership.This is Part 2 of Tess’s solo series on the psychology of work and why younger employees need more clarity, not more criticism.Chapter Timestamps00:00 Why early career hits harder than expected01:05 Learning who you are while being evaluated02:20 Why young professionals internalize stress03:05 High expectations, low control, constant comparison04:20 Why unclear environments create self-doubt04:50 What young employees should never normalize05:30 Why yelling at work should not be accepted06:15 Discomfort vs unhealthy environments06:50 How to separate mistakes from identity07:40 What leaders owe early-career employees Be sure to subscribe so you never miss a weekly episode. To learn more, or to Shop available resources, visit tessbrigham.com

Think you're not a morning person? Think again.This week, Tess sits down with Amy Landino, bestselling author, content creator, and founder of Vlog Boss Studios. Together, they blow up everything you think you know about morning routines, productivity, and what it actually means to start your day on your own terms.Amy's newly expanded book, Good Morning, Good Life, isn't about waking up at 5am or turning your morning into an Instagram aesthetic. It's about reclaiming ownership of your day before the world gets a vote, and her simple three-bucket framework (Movement, Mindfulness, and Mastery) makes that possible for anyone, in any season of life.Tess and Amy also get into the messy generational stuff: why Millennials were conditioned to believe "work harder" was always the answer, why a six-figure business might actually be the wrong goal, and the moment Amy told her dad she'd already made $90K that year and watched him go completely speechless.In this episode:Why your morning routine is probably built around someone else's agendaThe key difference between starting your day "on offense" vs. "on defense"Amy's three-bucket framework: Movement, Mindfulness & Mastery explained simplyThe real reason you're "not a morning person" (it's not what you think)Why a six-figure business might be the worst goal you're chasing right nowThe Millennial financial reality: student loans, a broken housing market, and boomer advice that no longer appliesHow self-compassion and accountability actually work together, not against each otherAmy Landino's book Good Morning, Good Life is available now. DM Amy on Instagram @AmyLandino the word "Tess" to receive her free Extraordinary Action Framework.CHAPTER TIMESTAMPS00:00 — Welcome & Amy Landino introduction01:00 — Amy's origin story: moving out at 18 and the "there's gotta be a better way" mindset04:00 — The wedding video that started everything — and how YouTube changed her life07:00 — What people get wrong about morning routines (hint: Instagram flex culture)09:30 — Checking email vs. checking your goals: offense vs. defense12:00 — Why you apologize for not replying fast enough — and why you need to stop13:15 — Is Good Morning, Good Life the Gen Z version of Miracle Morning? Tess makes the case16:45 — The three-bucket framework: Movement, Mindfulness & Mastery19:20 — Tess's morning confession: sitting with her dogs, and finally giving herself permission21:00 — "I'm not a morning person" — the #1 objection, completely reframed24:00 — "But I have kids" — excuse #2, and Amy's surprisingly honest answer28:45 — The Extraordinary Action Framework: DM Amy on Instagram to get it free29:20 — Self-compassion + accountability: why they're not opposites33:45 — Screw "realistic" — why shooting for the unrealistic actually makes sense34:45 — Hot take: Why Amy tells clients with six-figure businesses to just go get a job40:00 — Generational spotlight: Millennials as the internet's guinea pigs42:30 — Student loans, the housing market, and what Millennials actually inherited47:20 — Boomer advice vs. Millennial reality — a tension that's very, very real48:00 — The $90K moment: Amy's dad, and why the people who love you don't always know what's possible for youSUBSCRIBE to The Gen Mess with Tess podcast for weekly insights on workplace culture, generational challenges, and relationship advice.

Why does one vague comment from your boss stay in your head all day? Why does being left off a meeting invite suddenly feel personal? Why can work feel emotionally exhausting even when you’re technically “doing fine”?In this episode of The Gen Mess with Tess, Tess Brigham explains why work is never just about tasks, productivity, or performance—it’s psychological.From feedback and comparison to belonging, safety, and identity, Tess breaks down what’s happening beneath the surface when work stress feels bigger than the moment itself. She also explains why so many leaders misread performance issues that are actually clarity issues, communication issues, or nervous-system responses.If you’ve ever replayed a Slack message, questioned yourself after feedback, or wondered why Gen Z seems to experience work differently, this episode explains why.This is part 1 of a 2-part solo series on the emotional reality of work, leadership, and what younger employees are actually experiencing in today’s workplace. Part 2 will be published next week. Chapter Timestamps00:00 Why work is more psychological than most people realize01:10 Why your brain treats work stress like threat02:20 Why vague feedback feels personal03:15 Work, identity, and self-worth04:10 Why comparison intensifies workplace anxiety04:45 What leaders misunderstand about Gen Z retention06:00 Why Gen Z isn’t “too sensitive”07:10 Communication problems are often anxiety problems08:05 Why retention is a mental health issue09:00 The key question leaders should ask instead visit tessbrigham.com to learn more

In Episode 53 of The Gen Mess with Tess, Tess Brigham sits down with Amy Leneker, founder and CEO of the Center for Joyful Work, to explore why burnout keeps happening even to highly successful leaders who know better.Amy has helped more than 100,000 leaders and teams, including Fortune 100 companies, rethink leadership, workplace stress, and employee well-being. A former public policy executive and recovering workaholic, Amy shares how burning out twice forced her to confront the internal patterns that kept driving overwork, achievement, and chronic stress.Together, Tess and Amy unpack why burnout is not simply about workload; it is often tied to identity, workplace systems, leadership culture, and the stories people tell themselves about success.This conversation explores:why high performers often confuse overworking with worthhow burnout can repeat even after changing jobswhat workplace stress is doing to leadership pipelineswhy younger employees are redefining ambitionhow Gen Z experiences stress differently at workwhy recognition and appreciation matter more than many leaders realizethe three conditions that create joy at work: meaning, mattering, and momentumhow AI may force a new era of critical thinking in leadershipAmy also shares findings from her national workforce research showing that employees increasingly need joy at work to perform well, yet many leaders still operate inside systems that reward exhaustion instead of sustainability.For HR leaders, managers, and executives, this episode offers a practical framework for understanding employee burnout, generational tension, workplace stress, leadership development, and what healthy ambition may need to look like next.If your organization is asking why employees are disengaged, overwhelmed, or pulling back from leadership, this conversation explains what may be underneath it.Chapters with Timestamps00:00 – Why Amy Leneker Burned Out Twice02:14 – The Stress Story High Achievers Carry04:12 – Why Leadership Still Rewards Burnout06:45 – Why Joy Belongs in the Future of Leadership08:21 – Gen Z, Stress, and New Definitions of Work11:52 – Are Younger Workers Redefining Ambition?16:15 – The Three Conditions That Create Joy at Work20:23 – Why Gen Z Needs Appreciation More Than Leaders Think25:36 – The Exercise That Changed Amy’s Career31:13 – Parenting, Leadership, and Invisible Overwork35:01 – Why Workplace Systems Keep Breaking People40:13 – AI, Critical Thinking, and the Future of Work

In Episode 52 of The Gen Mess with Tess, Tess explores one of the most misunderstood workplace dynamics right now: why younger employees keep asking for transparency, and why many leaders misread that as entitlement.While transparency is often described as a Gen Z workplace preference, Tess argues it is something much deeper: a psychological response to growing up in a world where trust has become increasingly fragile.From financial instability and public institutional failures to social media fabrication, layoffs over Zoom, and the rise of AI, younger workers have developed a sharper need to understand what is real, what is changing, and what leaders are not saying.In this episode, Tess explains why transparency is no longer just a communication style. and is now the foundation of trust in modern organizations.Why Gen Z’s questions are often about safety, not defianceHow uncertainty activates worst-case thinking in the brainWhy silence from leadership often increases workplace anxietyThe difference between transparency and oversharingHow honesty improves motivation, engagement, and retentionWhy every generation benefits when leaders communicate clearlyFor HR leaders and managers, this episode offers a practical lens on why communication gaps create disengagement — and why explaining reality clearly may be one of the most powerful leadership tools available today.Because in today’s workplace, transparency is not a bonus. It is how trust gets built.Chapters with Timestamps00:00 – Why Transparency Keeps Coming Up in Every Workplace Conversation 02:20 – Why Gen Z Grew Up Distrusting Systems 04:38 – What the Brain Does When Information Is Missing 06:15 – Why Transparency Matters More Than Perfection 07:04 – A CEO’s Silence During Uncertainty 08:45 – How Honesty Calms the Nervous System 09:26 – Why Motivation Drops When Trust Is Unclear 10:45 – Transparency vs Oversharing 11:46 – Why Every Generation Needs More Clarity 13:10 – The Leadership Advantage of Honest Communication 14:04 – Final Takeaway: Transparency Rebuilds Trust

In Episode 51 of The Gen Mess with Tess, Tess is joined by Corrine Ishio, founder of My Working Soul, to explore a challenge many fast-growing companies face but rarely talk about: scaling the business faster than the culture can keep up.When organizations grow quickly, hiring often becomes reactive. Leaders focus on roles and results, while the human side of the company quietly gets lost. The result? Misalignment, disengagement, and teams that no longer feel connected to the mission that once energized them.Corrine shares her perspective from years working in talent, recruiting, and HR; helping founders and leadership teams rethink how they hire, communicate, and define culture during periods of rapid growth.In this conversation, Tess and Corrine explore:Why companies struggle to maintain culture as they scaleThe complicated role HR plays between employees and leadershipHow generational misunderstandings shape today’s workplaceWhy Gen Z communication patterns are confusing many managersThe influence of social media on workplace behavior and identityWhy purpose is becoming central to work in the AI eraThey also discuss how leaders can create healthier workplaces by focusing less on rigid definitions of culture and more on communication, self-awareness, and intentional hiring. Because when companies grow quickly, it’s easy to forget the most important part of any organization: the humans building it.Chapters (Timestamps)00:00 – Introduction to Corrine Ishio & My Working Soul 01:05 – Corrine’s Path Into HR & Human-Centered Work 04:00 – What HR Actually Does (vs. what people think it does) 07:00 – Why HR Often Feels Stuck Between Employees & Companies 11:00 – The “Human” Lens Inside Business Operations 13:00 – The Meaning Behind “My Working Soul” 17:00 – Why Culture Breaks When Companies Grow Quickly 20:30 – What a Healthy Workplace Actually Looks Like 23:00 – Communication Differences Across Generations 29:30 – Why Younger Workers Are Often Misunderstood 34:30 – Purpose, Work, and the AI Era 38:30 – Are Younger Employees Harder to Manage? 43:00 – Millennials, Social Media, and Cultural Fragmentation 49:00 – Safety, Identity, and the Digital Workplace